JP3665712B2 - シクロアルケン誘導体、その製造法および用途 - Google Patents

シクロアルケン誘導体、その製造法および用途 Download PDF

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Publication number: JP3665712B2
Authority: JP; Japan
Prior art keywords: group; compound; ethyl; carboxylate; cyclohexene
Prior art date: 1998-03-09
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP05963099A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000178246A (ja

Inventor

有三市森

雅幸伊井

克己伊藤

智幸北崎

順示山田

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Pharmaceutical Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-03-09

Filing date

1999-03-08

Publication date

2005-06-29

1999-03-08 Application filed by Takeda Pharmaceutical Co Ltd filed Critical Takeda Pharmaceutical Co Ltd

1999-03-08 Priority to JP05963099A priority Critical patent/JP3665712B2/ja

2000-06-27 Publication of JP2000178246A publication Critical patent/JP2000178246A/ja

2005-06-29 Application granted granted Critical

2005-06-29 Publication of JP3665712B2 publication Critical patent/JP3665712B2/ja

2019-03-08 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title description 33
150000001925 cycloalkenes Chemical class 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 61
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 40
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
KAIYAKPEHMHBCM-UHFFFAOYSA-N N-(2-chlorophenyl)-2-ethylcyclohex-2-ene-1-sulfonamide Chemical compound C(C)C1=CCCCC1S(NC1=C(C=CC=C1)Cl)(=O)=O KAIYAKPEHMHBCM-UHFFFAOYSA-N 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 250
125000001424 substituent group Chemical group 0.000 abstract description 106
125000001931 aliphatic group Chemical group 0.000 abstract description 49
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 38
125000000623 heterocyclic group Chemical group 0.000 abstract description 24
125000002029 aromatic hydrocarbon group Chemical group 0.000 abstract description 21
201000010099 disease Diseases 0.000 abstract description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 17
208000023275 Autoimmune disease Diseases 0.000 abstract description 9
239000003795 chemical substances by application Substances 0.000 abstract description 8
208000019622 heart disease Diseases 0.000 abstract description 7
229940002612 prodrug Drugs 0.000 abstract description 7
239000000651 prodrug Substances 0.000 abstract description 7
230000035939 shock Effects 0.000 abstract description 3
208000020446 Cardiac disease Diseases 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 612
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 231
-1 O2 - Chemical compound 0.000 description 209
230000002829 reductive effect Effects 0.000 description 110
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 105
238000005160 1H NMR spectroscopy Methods 0.000 description 104
238000006243 chemical reaction Methods 0.000 description 94
239000000243 solution Substances 0.000 description 94
238000000921 elemental analysis Methods 0.000 description 89
239000000203 mixture Substances 0.000 description 89
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 87
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 87
239000013078 crystal Substances 0.000 description 87
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 85
239000002904 solvent Substances 0.000 description 80
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 62
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
239000003480 eluent Substances 0.000 description 56
239000000843 powder Substances 0.000 description 56
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 51
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 50
HNDUKOBQKAFGCT-UHFFFAOYSA-N ethyl 2-chlorosulfonylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C(S(Cl)(=O)=O)CCCC1 HNDUKOBQKAFGCT-UHFFFAOYSA-N 0.000 description 49
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 46
238000000034 method Methods 0.000 description 43
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 42
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 42
238000010898 silica gel chromatography Methods 0.000 description 40
239000011541 reaction mixture Substances 0.000 description 38
SIIGGFCBVDNNNU-UHFFFAOYSA-N 2-ethoxycarbonylcyclohexene-1-sulfonic acid Chemical compound CCOC(=O)C1=C(S(O)(=O)=O)CCCC1 SIIGGFCBVDNNNU-UHFFFAOYSA-N 0.000 description 28
239000000047 product Substances 0.000 description 28
238000001816 cooling Methods 0.000 description 27
238000012360 testing method Methods 0.000 description 25
125000000217 alkyl group Chemical group 0.000 description 23
239000002198 insoluble material Substances 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
210000004027 cell Anatomy 0.000 description 20
125000005843 halogen group Chemical group 0.000 description 20
102000004127 Cytokines Human genes 0.000 description 19
108090000695 Cytokines Proteins 0.000 description 19
125000004432 carbon atom Chemical group C* 0.000 description 19
238000001035 drying Methods 0.000 description 19
239000002585 base Substances 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
239000012267 brine Substances 0.000 description 17
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
230000002401 inhibitory effect Effects 0.000 description 15
239000000126 substance Substances 0.000 description 15
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
238000004440 column chromatography Methods 0.000 description 14
229910052736 halogen Inorganic materials 0.000 description 14
238000001914 filtration Methods 0.000 description 13
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
229910052801 chlorine Inorganic materials 0.000 description 11
150000002367 halogens Chemical class 0.000 description 11
229910052943 magnesium sulfate Inorganic materials 0.000 description 11
235000019341 magnesium sulphate Nutrition 0.000 description 11
238000002360 preparation method Methods 0.000 description 11
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
108090001005 Interleukin-6 Proteins 0.000 description 10
102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
230000000694 effects Effects 0.000 description 10
239000002158 endotoxin Substances 0.000 description 10
VSOMGDDXCKLSIG-UHFFFAOYSA-N ethyl 6-[(2,4-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C=C1F VSOMGDDXCKLSIG-UHFFFAOYSA-N 0.000 description 10
238000003818 flash chromatography Methods 0.000 description 10
229920006008 lipopolysaccharide Polymers 0.000 description 10
238000003756 stirring Methods 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
206010040070 Septic Shock Diseases 0.000 description 9
102100040247 Tumor necrosis factor Human genes 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
239000008280 blood Substances 0.000 description 9
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
239000003814 drug Substances 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000000741 silica gel Substances 0.000 description 9
229910002027 silica gel Inorganic materials 0.000 description 9
229910052717 sulfur Inorganic materials 0.000 description 9
125000004434 sulfur atom Chemical group 0.000 description 9
MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
108060008682 Tumor Necrosis Factor Proteins 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 8
125000001309 chloro group Chemical group Cl* 0.000 description 8
229940126214 compound 3 Drugs 0.000 description 8
230000002757 inflammatory effect Effects 0.000 description 8
239000007788 liquid Substances 0.000 description 8
230000036303 septic shock Effects 0.000 description 8
239000007787 solid Substances 0.000 description 8
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
238000005406 washing Methods 0.000 description 8
108010002352 Interleukin-1 Proteins 0.000 description 7
239000002253 acid Substances 0.000 description 7
125000005037 alkyl phenyl group Chemical group 0.000 description 7
235000001014 amino acid Nutrition 0.000 description 7
150000001413 amino acids Chemical class 0.000 description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
150000007529 inorganic bases Chemical class 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000002994 raw material Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 6
XRAKCYJTJGTSMM-UHFFFAOYSA-N 2-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1Cl XRAKCYJTJGTSMM-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
229940125904 compound 1 Drugs 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
150000007530 organic bases Chemical class 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
238000000926 separation method Methods 0.000 description 6
229940124597 therapeutic agent Drugs 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 5
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 5
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
102100028452 Nitric oxide synthase, endothelial Human genes 0.000 description 5
101710090055 Nitric oxide synthase, endothelial Proteins 0.000 description 5
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
206010040047 Sepsis Diseases 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
125000005036 alkoxyphenyl group Chemical group 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
125000000392 cycloalkenyl group Chemical group 0.000 description 5
125000000753 cycloalkyl group Chemical group 0.000 description 5
230000016396 cytokine production Effects 0.000 description 5
230000032050 esterification Effects 0.000 description 5
238000005886 esterification reaction Methods 0.000 description 5
150000002170 ethers Chemical class 0.000 description 5
150000008282 halocarbons Chemical class 0.000 description 5
208000027866 inflammatory disease Diseases 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
210000002540 macrophage Anatomy 0.000 description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
150000007524 organic acids Chemical class 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
LSZZOBVNXASTKE-UHFFFAOYSA-M sodium;6-[(2,4-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C=C1F LSZZOBVNXASTKE-UHFFFAOYSA-M 0.000 description 5
150000003462 sulfoxides Chemical class 0.000 description 5
239000008096 xylene Substances 0.000 description 5
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 4
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VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
239000012980 RPMI-1640 medium Substances 0.000 description 4
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DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 4
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OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 4
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LEEIJTHMHDMWLJ-UHFFFAOYSA-N ethyl 6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C=C1Cl LEEIJTHMHDMWLJ-UHFFFAOYSA-N 0.000 description 4
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WDCDAAMJNUHOIY-UHFFFAOYSA-N ethyl acetate;2-propan-2-yloxypropane Chemical compound CCOC(C)=O.CC(C)OC(C)C WDCDAAMJNUHOIY-UHFFFAOYSA-N 0.000 description 4
125000001153 fluoro group Chemical group F* 0.000 description 4
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238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
150000007522 mineralic acids Chemical class 0.000 description 4
125000001624 naphthyl group Chemical group 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
230000003449 preventive effect Effects 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
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239000008107 starch Substances 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
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MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
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125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
JFDHANUKNFJNMM-UHFFFAOYSA-N ethyl 2-(phenylsulfamoyl)cyclohexene-1-carboxylate Chemical compound C1CCCC(C(=O)OCC)=C1S(=O)(=O)NC1=CC=CC=C1 JFDHANUKNFJNMM-UHFFFAOYSA-N 0.000 description 1
MDJSRTIQJICEQL-UHFFFAOYSA-N ethyl 2-[(2,4-difluorophenyl)sulfamoyl]cyclopentene-1-carboxylate Chemical compound C1CCC(C(=O)OCC)=C1S(=O)(=O)NC1=CC=C(F)C=C1F MDJSRTIQJICEQL-UHFFFAOYSA-N 0.000 description 1
RIQNQALNGPCKGS-UHFFFAOYSA-N ethyl 2-[(2-ethoxycarbonylcyclohex-2-en-1-yl)sulfonylamino]benzoate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC=C1C(=O)OCC RIQNQALNGPCKGS-UHFFFAOYSA-N 0.000 description 1
DGBCHOBHJMJNTF-UHFFFAOYSA-N ethyl 2-[(4-chloro-2-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound C1CCCC(C(=O)OCC)=C1S(=O)(=O)NC1=CC=C(Cl)C=C1F DGBCHOBHJMJNTF-UHFFFAOYSA-N 0.000 description 1
NYGYXDZUPZKQQD-UHFFFAOYSA-N ethyl 2-[(4-methoxyphenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound C1CCCC(C(=O)OCC)=C1S(=O)(=O)NC1=CC=C(OC)C=C1 NYGYXDZUPZKQQD-UHFFFAOYSA-N 0.000 description 1
JZNYKTFYDHOKCD-UHFFFAOYSA-N ethyl 2-oxo-5-phenylcyclohexane-1-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CC1C1=CC=CC=C1 JZNYKTFYDHOKCD-UHFFFAOYSA-N 0.000 description 1
DJUARJDPNNUMHF-UHFFFAOYSA-N ethyl 2-sulfanylcycloheptene-1-carboxylate Chemical compound CCOC(=O)C1=C(S)CCCCC1 DJUARJDPNNUMHF-UHFFFAOYSA-N 0.000 description 1
FYEYSNRFEGSEEH-UHFFFAOYSA-N ethyl 2-sulfanylcyclopentene-1-carboxylate Chemical compound CCOC(=O)C1=C(S)CCC1 FYEYSNRFEGSEEH-UHFFFAOYSA-N 0.000 description 1
CKPZSGYOJUUUMX-UHFFFAOYSA-N ethyl 3,3-dimethyl-6-oxocyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(C)(C)CCC1=O CKPZSGYOJUUUMX-UHFFFAOYSA-N 0.000 description 1
LRFXXNOHAUCGCX-UHFFFAOYSA-N ethyl 3-bromo-6-[(2,4-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(Br)CCC1S(=O)(=O)NC1=CC=C(F)C=C1F LRFXXNOHAUCGCX-UHFFFAOYSA-N 0.000 description 1
KYRMEZYRTHPOOP-UHFFFAOYSA-N ethyl 3-tert-butyl-6-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(C(C)(C)C)CCC1S(=O)(=O)NC1=CC=C(F)C=C1Cl KYRMEZYRTHPOOP-UHFFFAOYSA-N 0.000 description 1
RECMFZRZYYRWGP-UHFFFAOYSA-N ethyl 3-tert-butyl-6-oxocyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(C(C)(C)C)CCC1=O RECMFZRZYYRWGP-UHFFFAOYSA-N 0.000 description 1
JITMXPHWSQLOFO-UHFFFAOYSA-N ethyl 5,5-dimethyl-2-sulfanylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C(S)CCC(C)(C)C1 JITMXPHWSQLOFO-UHFFFAOYSA-N 0.000 description 1
KGVRDJRPADGOGP-UHFFFAOYSA-N ethyl 5-[(2,4-difluorophenyl)sulfamoyl]cyclopentene-1-carboxylate Chemical compound CCOC(=O)C1=CCCC1S(=O)(=O)NC1=CC=C(F)C=C1F KGVRDJRPADGOGP-UHFFFAOYSA-N 0.000 description 1
VJKDBRHDGCPRBZ-UHFFFAOYSA-N ethyl 5-[(2-chloro-4-fluorophenyl)sulfamoyl]cyclopentene-1-carboxylate Chemical compound CCOC(=O)C1=CCCC1S(=O)(=O)NC1=CC=C(F)C=C1Cl VJKDBRHDGCPRBZ-UHFFFAOYSA-N 0.000 description 1
UUZAYHPBPFRMMJ-UHFFFAOYSA-N ethyl 5-phenyl-2-sulfanylcyclohexene-1-carboxylate Chemical compound C1C(C(=O)OCC)=C(S)CCC1C1=CC=CC=C1 UUZAYHPBPFRMMJ-UHFFFAOYSA-N 0.000 description 1
KKPNCNSAGIYBKS-UHFFFAOYSA-N ethyl 5-tert-butyl-2-sulfanylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=C(S)CCC(C(C)(C)C)C1 KKPNCNSAGIYBKS-UHFFFAOYSA-N 0.000 description 1
QVLIXIOMZHQBDD-UHFFFAOYSA-N ethyl 6-(phenylsulfamoyl)cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC=C1 QVLIXIOMZHQBDD-UHFFFAOYSA-N 0.000 description 1
BHYRGRFJGOPWEW-UHFFFAOYSA-N ethyl 6-[(2,3,4-trifluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C(F)=C1F BHYRGRFJGOPWEW-UHFFFAOYSA-N 0.000 description 1
HSZXFGDFIVVLKP-UHFFFAOYSA-N ethyl 6-[(2,3-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC(F)=C1F HSZXFGDFIVVLKP-UHFFFAOYSA-N 0.000 description 1
TWYGKUPLZKSOHO-UHFFFAOYSA-N ethyl 6-[(2,4,5-trifluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC(F)=C(F)C=C1F TWYGKUPLZKSOHO-UHFFFAOYSA-N 0.000 description 1
FLSDSYNBODHRCV-UHFFFAOYSA-N ethyl 6-[(2,4-dichlorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(Cl)C=C1Cl FLSDSYNBODHRCV-UHFFFAOYSA-N 0.000 description 1
CANLDVNPUSKNPF-UHFFFAOYSA-N ethyl 6-[(2,4-difluorophenyl)sulfamoyl]-3,3-dimethylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(C)(C)CCC1S(=O)(=O)NC1=CC=C(F)C=C1F CANLDVNPUSKNPF-UHFFFAOYSA-N 0.000 description 1
MZJHJPJCEZQPQQ-UHFFFAOYSA-N ethyl 6-[(2,4-difluorophenyl)sulfamoyl]-3-phenylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(C=2C=CC=CC=2)CCC1S(=O)(=O)NC1=CC=C(F)C=C1F MZJHJPJCEZQPQQ-UHFFFAOYSA-N 0.000 description 1
PFBWJPWPTITSGR-UHFFFAOYSA-N ethyl 6-[(2,5-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC(F)=CC=C1F PFBWJPWPTITSGR-UHFFFAOYSA-N 0.000 description 1
ALJUCLRIWALRLS-UHFFFAOYSA-N ethyl 6-[(2,6-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=C(F)C=CC=C1F ALJUCLRIWALRLS-UHFFFAOYSA-N 0.000 description 1
INTUQDAJAOIFRT-UHFFFAOYSA-N ethyl 6-[(2-acetyloxyphenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC=C1OC(C)=O INTUQDAJAOIFRT-UHFFFAOYSA-N 0.000 description 1
DSTOCVBALDHISX-UHFFFAOYSA-N ethyl 6-[(2-bromo-4-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C=C1Br DSTOCVBALDHISX-UHFFFAOYSA-N 0.000 description 1
YSEMBDNHOINHLO-UHFFFAOYSA-N ethyl 6-[(2-chloro-4-cyanophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(C#N)C=C1Cl YSEMBDNHOINHLO-UHFFFAOYSA-N 0.000 description 1
QWWGKURDBXRXPB-UHFFFAOYSA-N ethyl 6-[(2-chloro-4-fluorophenyl)sulfamoyl]-3,3-dimethylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(C)(C)CCC1S(=O)(=O)NC1=CC=C(F)C=C1Cl QWWGKURDBXRXPB-UHFFFAOYSA-N 0.000 description 1
DHDBGZFSLVOGSI-UHFFFAOYSA-N ethyl 6-[(2-chloro-4-fluorophenyl)sulfamoyl]-3-phenylcyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CC(C=2C=CC=CC=2)CCC1S(=O)(=O)NC1=CC=C(F)C=C1Cl DHDBGZFSLVOGSI-UHFFFAOYSA-N 0.000 description 1
HWQURAAFPCRGQP-UHFFFAOYSA-N ethyl 6-[(2-ethylphenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC=C1CC HWQURAAFPCRGQP-UHFFFAOYSA-N 0.000 description 1
FAGALKGVUMNBGH-UHFFFAOYSA-N ethyl 6-[(2-fluoro-4-methylphenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(C)C=C1F FAGALKGVUMNBGH-UHFFFAOYSA-N 0.000 description 1
QUXKSZOGCGTJHX-UHFFFAOYSA-N ethyl 6-[(2-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC=C1F QUXKSZOGCGTJHX-UHFFFAOYSA-N 0.000 description 1
GZZNKNBLRCCOCD-UHFFFAOYSA-N ethyl 6-[(3,4-difluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C(F)=C1 GZZNKNBLRCCOCD-UHFFFAOYSA-N 0.000 description 1
PXCWEJCDNIBFMX-UHFFFAOYSA-N ethyl 6-[(3-chlorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC(Cl)=C1 PXCWEJCDNIBFMX-UHFFFAOYSA-N 0.000 description 1
LXYYJORRLSAGMW-UHFFFAOYSA-N ethyl 6-[(3-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC(F)=C1 LXYYJORRLSAGMW-UHFFFAOYSA-N 0.000 description 1
AOLZBTCZZRODHR-UHFFFAOYSA-N ethyl 6-[(4-bromo-2-chlorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(Br)C=C1Cl AOLZBTCZZRODHR-UHFFFAOYSA-N 0.000 description 1
IRADMVDZNCTKSI-UHFFFAOYSA-N ethyl 6-[(4-bromo-2-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(Br)C=C1F IRADMVDZNCTKSI-UHFFFAOYSA-N 0.000 description 1
KKVCXFAANICNJV-UHFFFAOYSA-N ethyl 6-[(4-chloro-2-fluorophenyl)-methylsulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)N(C)C1=CC=C(Cl)C=C1F KKVCXFAANICNJV-UHFFFAOYSA-N 0.000 description 1
HSJAXXFQYZFTAT-UHFFFAOYSA-N ethyl 6-[(4-chlorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(Cl)C=C1 HSJAXXFQYZFTAT-UHFFFAOYSA-N 0.000 description 1
GOJUDIIYNWBBRZ-UHFFFAOYSA-N ethyl 6-[(4-fluoro-2-methylphenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C=C1C GOJUDIIYNWBBRZ-UHFFFAOYSA-N 0.000 description 1
LWIFMCAYFYWZDB-UHFFFAOYSA-N ethyl 6-[(4-fluorophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(F)C=C1 LWIFMCAYFYWZDB-UHFFFAOYSA-N 0.000 description 1
JVGWVYODDMLHLR-UHFFFAOYSA-N ethyl 6-[(4-nitrophenyl)sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C([N+]([O-])=O)C=C1 JVGWVYODDMLHLR-UHFFFAOYSA-N 0.000 description 1
SAOGCGBSKJKUJQ-UHFFFAOYSA-N ethyl 6-[[2-(trifluoromethoxy)phenyl]sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC=C1OC(F)(F)F SAOGCGBSKJKUJQ-UHFFFAOYSA-N 0.000 description 1
TYURXESONCEUBO-UHFFFAOYSA-N ethyl 6-[[2-(trifluoromethyl)phenyl]sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=CC=C1C(F)(F)F TYURXESONCEUBO-UHFFFAOYSA-N 0.000 description 1
OBQYTCZKVZMANL-UHFFFAOYSA-N ethyl 6-[[2-chloro-4-[(2-ethoxy-2-oxoethyl)carbamoyl]phenyl]sulfamoyl]cyclohexene-1-carboxylate Chemical compound ClC1=CC(C(=O)NCC(=O)OCC)=CC=C1NS(=O)(=O)C1C(C(=O)OCC)=CCCC1 OBQYTCZKVZMANL-UHFFFAOYSA-N 0.000 description 1
RUZJYUUHUOCUHL-UHFFFAOYSA-N ethyl 6-[[2-fluoro-4-(1,2,4-triazol-1-yl)phenyl]sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(N2N=CN=C2)C=C1F RUZJYUUHUOCUHL-UHFFFAOYSA-N 0.000 description 1
VBQHDPCQGBIKGB-UHFFFAOYSA-N ethyl 6-[[4-(tetrazol-1-yl)phenyl]sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(N2N=NN=C2)C=C1 VBQHDPCQGBIKGB-UHFFFAOYSA-N 0.000 description 1
JWRDINJYKLEKIC-UHFFFAOYSA-N ethyl 6-[[4-(tetrazol-2-yl)phenyl]sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(N2N=NC=N2)C=C1 JWRDINJYKLEKIC-UHFFFAOYSA-N 0.000 description 1
JJPDSKFMDIZJRV-UHFFFAOYSA-N ethyl 6-[[4-(triazol-2-yl)phenyl]sulfamoyl]cyclohexene-1-carboxylate Chemical compound CCOC(=O)C1=CCCCC1S(=O)(=O)NC1=CC=C(N2N=CC=N2)C=C1 JJPDSKFMDIZJRV-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/14—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
- C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Cardiology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Transplantation (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Rheumatology (AREA)
Toxicology (AREA)
Heart & Thoracic Surgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Thiazole And Isothizaole Compounds (AREA)
Steroid Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Silicon Compounds (AREA)

JP05963099A 1998-03-09 1999-03-08 シクロアルケン誘導体、その製造法および用途 Expired - Lifetime JP3665712B2 (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP05963099A JP3665712B2 (ja)	1998-03-09	1999-03-08	シクロアルケン誘導体、その製造法および用途

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
JP5649298		1998-03-09
JP10-56492		1998-03-09
JP28436298		1998-10-06
JP10-284362		1998-10-06
JP05963099A JP3665712B2 (ja)	1998-03-09	1999-03-08	シクロアルケン誘導体、その製造法および用途

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
JP2005026914A Division JP4342453B2 (ja)	1998-03-09	2005-02-02	シクロアルケン誘導体、その製造法および用途

Publications (2)

Publication Number	Publication Date
JP2000178246A JP2000178246A (ja)	2000-06-27
JP3665712B2 true JP3665712B2 (ja)	2005-06-29

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ID=26397446

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Application Number	Title	Priority Date	Filing Date
JP05963099A Expired - Lifetime JP3665712B2 (ja)	1998-03-09	1999-03-08	シクロアルケン誘導体、その製造法および用途
JP2005026914A Expired - Fee Related JP4342453B2 (ja)	1998-03-09	2005-02-02	シクロアルケン誘導体、その製造法および用途

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JP2005026914A Expired - Fee Related JP4342453B2 (ja)	1998-03-09	2005-02-02	シクロアルケン誘導体、その製造法および用途

Country Status (19)

Country	Link
US (1)	US6495604B1 (de)
EP (2)	EP1063228B1 (de)
JP (2)	JP3665712B2 (de)
KR (4)	KR100492098B1 (de)
CN (1)	CN100432049C (de)
AT (1)	ATE287393T1 (de)
AU (1)	AU747521B2 (de)
BR (1)	BR9908610A (de)
CA (1)	CA2320467C (de)
DE (1)	DE69923300T2 (de)
DK (1)	DK1063228T5 (de)
ES (1)	ES2232114T3 (de)
HU (1)	HU230061B1 (de)
ID (1)	ID25649A (de)
NO (1)	NO326426B1 (de)
NZ (1)	NZ505874A (de)
PT (1)	PT1063228E (de)
RU (1)	RU2214398C2 (de)
WO (1)	WO1999046242A1 (de)

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AU1553001A (en) *	1999-11-29	2001-06-12	Takeda Chemical Industries Ltd.	Process for the production of optically active cyclohexene derivatives and intermediates therefor
US7105572B2 (en)	2000-02-04	2006-09-12	Takeda Pharmaceutical Company Limited	Stable emulsion compositions
JP4863553B2 (ja) *	2000-02-04	2012-01-25	武田薬品工業株式会社	安定な乳化組成物
AU2001278705A1 (en)	2000-08-10	2002-02-25	Takeda Chemical Industries Ltd.	Pharmaceutical composition
JP4922507B2 (ja) *	2000-08-10	2012-04-25	武田薬品工業株式会社	医薬組成物
EP1334966B1 (de)	2000-10-18	2011-05-04	Takeda Pharmaceutical Company Limited	Verfahren zur herstellung von optisch aktiven sulfonamiden und zwischenprodukte zur deren synthese
CA2431206C (en) *	2000-12-08	2009-09-01	Takeda Chemical Industries, Ltd.	Combination drugs containing anti-sepsis cycloalkene compound
US7579325B2 (en)	2001-03-21	2009-08-25	Eisai R & D Management Co., Ltd.	Drugs containing reduced of vitamin B2
EP1420783A4 (de) *	2001-08-03	2009-09-30	Takeda Pharmaceutical	Stabile emulsionszusammensetzung
EP1495756A4 (de) *	2002-04-08	2009-10-28	Takeda Pharmaceutical	Therapeutikum zur prävention schwerer sepsis
DE602004031759D1 (de)	2003-12-03	2011-04-21	Boehringer Ingelheim Pharma	1,2,3-triazolamidderivate als inhibitoren der cytokinproduktion
TWI462745B (zh) *	2005-04-28	2014-12-01	Takeda Pharmaceutical	安定的乳化組成物
JP4195074B2 (ja) *	2005-09-14	2008-12-10	第一三共株式会社	置換シクロアルケン誘導体
JP4962982B2 (ja)	2006-03-30	2012-06-27	国立大学法人広島大学	スクリーニング方法
WO2007123186A1 (ja)	2006-04-20	2007-11-01	Takeda Pharmaceutical Company Limited	医薬
EP2018855A1 (de) *	2006-05-15	2009-01-28	Takeda Pharmaceutical Company Limited	Pharmazeutisches mittel
JPWO2008004673A1 (ja)	2006-07-07	2009-12-10	武田薬品工業株式会社	シクロアルケン誘導体、その製造法および用途
JP2008260760A (ja) *	2007-03-12	2008-10-30	Daiichi Sankyo Co Ltd	置換シクロアルケン誘導体を含有する医薬組成物
UY33203A (es)	2010-01-27	2011-08-31	Takeda Pharmaceutical	Medicamento que suprime (o mitiga) varios síntomas neurológicos originados por un trastorno del nervio periférico inducido por un agente anticancerígeno
JP5778161B2 (ja)	2010-09-24	2015-09-16	第一三共株式会社	置換シクロアルケン誘導体の結晶
CA2915793A1 (en) *	2012-07-03	2014-01-09	Jay Pravda	Methods for treating, diagnosing and/or monitoring progression of oxo associated states
US9364438B2 (en)	2012-09-26	2016-06-14	Takeda Pharmaceutical Company Limited	Process for producing solid particles
TW201704206A (zh) *	2015-05-08	2017-02-01	武田藥品工業股份有限公司	環狀化合物
JP7029400B2 (ja)	2016-09-09	2022-03-03	武田薬品工業株式会社	環状化合物
CN110352189A (zh) *	2017-02-24	2019-10-18	景凯生物科技股份有限公司	用于预防及/或治疗自体免疫、发炎或感染相关障碍的磺酰胺或酰胺化合物、组合物与方法

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AU653279B2 (en) *	1991-12-30	1994-09-22	Sanofi	Novel 2-saccharinylmethyl heterocyclic carboxylates useful as proteolytic enzyme inhibitors and compositions and method of use thereof
US5576016A (en)	1993-05-18	1996-11-19	Pharmos Corporation	Solid fat nanoemulsions as drug delivery vehicles
FI963297A7 (fi)	1994-02-25	1996-10-18	Takeda Chemical Industries Ltd	Antifungaalisia triatsolijohdannaisia sisältävät emulsiot
JPH08109165A (ja) *	1994-08-18	1996-04-30	Chugai Pharmaceut Co Ltd	一酸化窒素合成酵素阻害作用を有するアミノ酸誘導体
EP0776886A4 (de) *	1994-08-18	1999-05-12	Chugai Pharmaceutical Co Ltd	Aminosäurenderivat mit stickstoffmonoxidsynthetase inhibierender aktivität
CN100432049C (zh)	1998-03-09	2008-11-12	武田药品工业株式会社	环烯衍生物、其制造方法和用途
US7105572B2 (en)	2000-02-04	2006-09-12	Takeda Pharmaceutical Company Limited	Stable emulsion compositions

1999
- 1999-03-08 CN CNB998029521A patent/CN100432049C/zh not_active Expired - Lifetime
- 1999-03-08 KR KR10-2000-7009764A patent/KR100492098B1/ko not_active Expired - Lifetime
- 1999-03-08 EP EP99907879A patent/EP1063228B1/de not_active Expired - Lifetime
- 1999-03-08 WO PCT/JP1999/001103 patent/WO1999046242A1/ja not_active Ceased
- 1999-03-08 US US09/622,392 patent/US6495604B1/en not_active Expired - Lifetime
- 1999-03-08 AT AT99907879T patent/ATE287393T1/de active
- 1999-03-08 PT PT99907879T patent/PT1063228E/pt unknown
- 1999-03-08 ES ES99907879T patent/ES2232114T3/es not_active Expired - Lifetime
- 1999-03-08 AU AU27464/99A patent/AU747521B2/en not_active Ceased
- 1999-03-08 HU HU0101192A patent/HU230061B1/hu not_active IP Right Cessation
- 1999-03-08 BR BR9908610-7A patent/BR9908610A/pt not_active IP Right Cessation
- 1999-03-08 RU RU2000125568/04A patent/RU2214398C2/ru not_active IP Right Cessation
- 1999-03-08 DK DK99907879T patent/DK1063228T5/da active
- 1999-03-08 KR KR1020067001730A patent/KR100779889B1/ko not_active Expired - Fee Related
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- 1999-03-08 JP JP05963099A patent/JP3665712B2/ja not_active Expired - Lifetime
- 1999-03-08 ID IDW20001736A patent/ID25649A/id unknown
- 1999-03-08 DE DE69923300T patent/DE69923300T2/de not_active Expired - Lifetime
- 1999-03-08 EP EP05000768A patent/EP1524263A1/de not_active Withdrawn
2000
- 2000-09-08 NO NO20004485A patent/NO326426B1/no not_active IP Right Cessation
2005
- 2005-02-02 JP JP2005026914A patent/JP4342453B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CN1291184A (zh)	2001-04-11
DK1063228T5 (da)	2009-06-15
AU747521C (en)	1999-09-27
JP4342453B2 (ja)	2009-10-14
DE69923300D1 (de)	2005-02-24
JP2000178246A (ja)	2000-06-27
EP1524263A1 (de)	2005-04-20
CA2320467C (en)	2010-05-04
NO326426B1 (no)	2008-12-01
KR100577044B1 (ko)	2006-05-08
CA2320467A1 (en)	1999-09-16
WO1999046242A1 (en)	1999-09-16
DK1063228T3 (da)	2005-04-25
KR20050026075A (ko)	2005-03-14
PL342826A1 (en)	2001-07-02
HUP0101192A3 (en)	2003-09-29
EP1063228A1 (de)	2000-12-27
ID25649A (id)	2000-10-19
PT1063228E (pt)	2005-05-31
NO20004485L (no)	2000-09-08
US6495604B1 (en)	2002-12-17
AU2746499A (en)	1999-09-27
KR20010034555A (ko)	2001-04-25
ATE287393T1 (de)	2005-02-15
EP1063228B1 (de)	2005-01-19
ES2232114T3 (es)	2005-05-16
RU2214398C2 (ru)	2003-10-20
BR9908610A (pt)	2000-12-05
CN100432049C (zh)	2008-11-12
KR100492098B1 (ko)	2005-06-01
JP2005232168A (ja)	2005-09-02
HUP0101192A2 (hu)	2001-08-28
HU230061B1 (hu)	2015-06-29
KR100779889B1 (ko)	2007-11-28
NO20004485D0 (no)	2000-09-08
KR20060017921A (ko)	2006-02-27
AU747521B2 (en)	2002-05-16
EP1063228A4 (de)	2001-08-08
DE69923300T2 (de)	2006-01-05
KR20050071719A (ko)	2005-07-07
NZ505874A (en)	2003-09-26
HK1031723A1 (en)	2001-06-22

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Publication	Publication Date	Title
JP3665712B2 (ja)	2005-06-29	シクロアルケン誘導体、その製造法および用途
US7417059B2 (en)	2008-08-26	Substituted aromatic-ring compounds, process for producing the same and use
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JP4012389B2 (ja)	2007-11-21	スルホンアミド基を有する光学活性体の製造法およびその合成中間体
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JPWO2001010826A1 (ja)	2003-03-04	置換芳香環化合物、その製造法および用途
HK1031723C (en)	2005-05-27	Cycloalkene derivatives, process for producing the same, and use
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JP4145042B2 (ja)	2008-09-03	併用薬
MXPA00008357A (en)	2001-12-04	Cycloalkene derivatives, process for producing the same, and use
JP2001261557A (ja)	2001-09-26	溶解性または安定性が改善された注射用組成物